STEREOSELECTIVITY IN THE 1,4-ADDITION REACTION OF ORGANOCOPPER REAGENTS TO ETHYL 3-[(S)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YL]PROPENOATE

Authors
NILSSON K ULLENIUS C
Citation
K. Nilsson et C. Ullenius, STEREOSELECTIVITY IN THE 1,4-ADDITION REACTION OF ORGANOCOPPER REAGENTS TO ETHYL 3-[(S)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YL]PROPENOATE, Tetrahedron, 50(46), 1994, pp. 13173-13180
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
46
Year of publication
1994
Pages
13173 - 13180
Database
ISI
SICI code
0040-4020(1994)50:46<13173:SIT1RO>2.0.ZU;2-T
Abstract
The chemo- and stereoselectivity in reactions with E and Z isomers of ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate, 1 and 2, are str ongly dependent on the composition of the organocopper reagent. Synthe tically useful yields and stereoselectivities are obtained with reagen ts of good nucleophilicity, e.g. RCu-TMSI-LiI. A transition state mode l based on copper-alkene pi-complex formation with intramolecular chel ation of the gamma-oxygen to lithium cluster can be used to rationaliz e the observed anti selectivity.